1. Field of the Invention
This invention relates to novel phosphoroamidothioate and phosphoroamidodithioate compounds, to compositions thereof which are useful as pesticides, for example, as arthropodicides (that is, insecticides and acaricides), nematocides, and fungicides, and to a method of controlling pests, such as insects, acarids, nematodes, and fungi. The compounds are effective when applied by soil application techniques and by foliar application techniques.
2. Description of the Prior Art
Ollinger, U.S. Pat. No. 4,263,288, issued Apr. 21, 1981, discloses acaricidal, insecticidal, and nematocidal phosphoroamidothioates having the formula EQU [(A--N.dbd.C(R)](N(R.sup.1)]P(.dbd.X)(R.sup.2)(SR.sup.3)
wherein
A is aryl, PA0 R is hydrogen or alkyl, PA0 R.sup.1 is alkyl, cycloalkyl, alkenyl, alkynyl or aralkyl, PA0 R.sup.2 is alkylthio, aryloxy, or amino, PA0 R.sup.3 is alkyl, and PA0 X is O or S. PA0 R.sup.1 and R.sup.2 are alkyl, alkenyl, diaryl, alkaryl, or aralkyl groups; PA0 X and X.sup.1 are O, S, or Se; and PA0 n is an integer from 2-9. PA0 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5) alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or di-alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms or, when X and Y are both S; CH.sub.3 ; or PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is hydrogen; PA0 X, Y and Z are independently O or S provided that both X and Y are not O at the same time except that, in the case that X and Y are both O and Z is S, then R.sup.1 is n--C.sub.3 H.sub.7 or s--C.sub.4 H.sub.9, R.sup.2 is s--C.sub.4 H.sub.9, R.sup.3 is H, and R.sup.4 is CH.sub.3. PA0 R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4) alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups; PA0 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5) alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or di-alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is hydrogen; PA0 R.sup.1 is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl; PA0 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5) alkyl, phenyl or benzyl; PA0 R.sup.3 is hydrogen, methyl, or trifluoromethyl; and PA0 R.sup.4 is methyl, ethyl, n-propyl propenyl or unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different (C.sub.1 -C.sub.3) alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups. PA0 R.sup.1 is methyl, ethyl, or 2,2,2-trifluoroethyl; PA0 R.sup.2 is n-propyl, 3-pentyl, or 1-methylpropyl; PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is methyl, ethyl, or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C.sub.1 -C.sub.3) alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups; PA0 X and Y are, independently, O or S; and PA0 Z is O. PA0 (H.sub.5 C.sub.2 O)P(S) (S sec--C.sub.4 H.sub.9) (N(C.sub.2 H.sub.5) (CHO)); PA0 (H.sub.5 C.sub.2 O)P(S) (S sec--C.sub.4 H.sub.9) (N(C.sub.2 H.sub.5) (CHS)); PA0 (H.sub.5 C.sub.2 O)P(S) (S sec--C.sub.4 H.sub.9) (N(CH.sub.3) (CHO)); PA0 (H.sub.5 C.sub.2 O)P(O) (S sec--C.sub.4 H.sub.9) (N(C.sub.2 H.sub.5) (CHS)); and PA0 (H.sub.5 C.sub.2 O)P(S) (S sec--C.sub.4 H.sub.9) (N(CH.sub.2 C.sub.6 H.sub.4 CF.sub.3 --3) (CHO)). PA0 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5) alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or di-alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is substituted (C.sub.1 -C.sub.7) alkyl wherein the substituent can be one to three of the same or different phenylcarbonyl, carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono- or di-alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA0 X, Y and Z are each O. PA0 R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups; PA0 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5) alkyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or di-alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is substituted (C.sub.1 -C.sub.7) alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, alkylthio, amino, or mono- or di-alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA0 R.sup.1 is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl, or benzyl; PA0 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5) alkyl, phenyl, or benzyl; PA0 R.sup.3 is hydrogen; and PA0 R.sup.4 is unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups. PA0 R.sup.1 is methyl, ethyl, or 2,2,2-trifluoroethyl; PA0 R.sup.2 is n-propyl, 3-pentyl, or 1-methylpropyl; PA0 R.sup.3 hydrogen; and PA0 R.sup.4 is unsubstituted or substituted benzyl wherein the substituent can be from one to two (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups. PA0 N-methyl-N-hydrogenthiocarbonyl-O-ethyl-S-n-butyl phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-n-butyl phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-n-butyl phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(2-methylpropyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(1-pentyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(2-methylbutyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(1-methylbutyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(3-methylbutyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(2,2-dimethylpropyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(2-methoxyethyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenocarbonyl O-ethyl S-(3-nitropropyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(3-nitro propyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl) phosphoroamidothioate PA0 N-methyl-N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl) phosphoroamidodithioate PA0 N-methyl-N-hydrogencarbonyl O-ethyl S-(2-cyanoethyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(3-chloropropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(2-fluoroethyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthiomethyl phosphoroamidothioate PA0 N-methyl N-hydrogentiocarbonyl O-ethyl S-ethylthioethyl phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-ethylthiomethyl phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl] phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl] phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl] phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(2-bromoallyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl) phosphoroamidothioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(3-butenyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(2-butenyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(5-hexenyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-propargyl phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-phenyl phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(1-phenylethyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-ethyl S-(5-phenyl-1-pentyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-phenyl-1-pentyl) phosphoroamidodithioate PA0 N-methyl N-methylcarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-methyl N-butylcarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-heptyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidothioate PA0 N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(3-methoxypropyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidothioate PA0 N-(3-methoxypropyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(3-methoxylpropyl) N-hydrogencarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(3-chloropropyl) N-hydrogencarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(3-chloropropyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidothioate PA0 N-(3-chloropropyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(2-fluoroethyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidothioate PA0 N-(2-fluoroethyl) N-hydrogencarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(2-butenyl) N-hydrogencarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(2-butenyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidothioate PA0 N-(2-butenyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(5-hexenyl) N-hydrogencarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(5-hexenyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidodithioate PA0 N-(5-hexenyl) N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl) phosphoroamidothioate PA0 N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1 methylpropyl) phosphoroamidothioate PA0 N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1 methylpropyl) phosphoroamidodithioate PA0 N-[(2-carboethoxy)-1-propenyl]N-hydrogencarbonyl O-ethyl S-(1 methylpropyl) phosphoroamidodithioate PA0 N-(3-hexyn-1-yl) N-hydrogencarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-(3-hexyn-1-yl) N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-(3-hexyn-1-yl) N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-phenyl N-hydrogencarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-p-chlorobenzyl N-hydrogencarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-(5-phenyl-1-pentyl) N-hydrogencarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-(5-phenyl-1-pentyl) N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-(5-phenyl-1-pentyl) N-hydrogenthiocarbonyl O-ethyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl-O-propyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-propyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-propyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-n-butyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-(2,2,2-trifluoroethyl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl) S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-allyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-allyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-allyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-(3-butenyl) S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-(3-butenyl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-(3-butenyl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-propargyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-(3-hexyn-1-yl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-(3-hexyn-1-yl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-phenyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-phenyl S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-phenyl S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogencarbonyl O-(2-phenylethyl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl) S-(1 -methylpropyl) phosphoroamidothioate PA0 N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl) S-(1 -methylpropyl) phosphoroamidodithioate PA0 S,S'-dibutyl N-hydrogenthiocarbonyl N-methyl phosphoroamidodithioate PA0 N-hydrogencarbonyl N,S-dimethyl S'-(1-methylpropyl) phosphoroamidotrithioate PA0 N-methylthiocarbonyl N,S,S'-tripropyl phosphoroamidodithioate PA0 S-ethyl N-heptyl S'-propyl N-trifluoromethylcarbonyl phosphoroamidotrithioate PA0 S-methyl S'-pentyl N-propyl N-propoxymethylthiocarbonyl phosphoroamidodithioate PA0 S-ethyl S'-(2-hexenyl) N-methyl N-trifluoromethylthiocarbonyl phosphoroamidotrithioate PA0 N-ethyl S-methyl S'-(2-propenyl) N-trifluoromethyl phosphoroamidotrithioate PA0 N-ethyl N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl) phosphoroamidodithioate PA0 N-ethyl N-hydrogenthiocarbonyl S-(1-methylpropyl) S'-(2-propynyl) phosphoroamidotrithioate PA0 N-ethyl S-(2-hexynyl) N-hydrogencarbonyl S'-(1-methylpropyl) phosphoroamidotrithioate PA0 S-(2-fluorobutyl) N-hydrogenthiocarbonyl N-methyl S'-(1-methylethyl) phosphoroamidodithioate PA0 N-methylcarbonyl S-phenyl N,S'-dipropyl phosphoroamidotrithioate PA0 S-benzyl S'-(1-ethylpropyl) N-hydrogenthiocarbonyl N-methyl phosphorotriamidothiate PA0 S-butyl N-ethyl N-methylcarbonyl S'-(5-phenylpentyl) phosphoroamidotrithioate PA0 S-butyl N-methylthiocarbonyl N-(2-propenyl) S'-propyl phosphoroamidodithioate PA0 N-(3-hexenyl) N-hydrogencarbonyl S,S'-dipropyl phosphoroamidotrithioate PA0 N-(3-hexynyl) N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl) phosphoroamidodithioate PA0 S-ethyl N,S'-di-(3-propynyl) N-trifluoromethylthiocarbonyl phosphoroamidodithioate PA0 N-benzyl N-hydrogenthiocarbonyl S,S'-dipropyl phosphoroamidotrithioate PA0 N-(carbomethoxymethyl)-N-hydrogencarbonyl O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA0 N-(carboethoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphor oamidodithioate PA0 N-(cyanomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido dithioate PA0 N-(methoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroami dothioate PA0 N-(methylthiomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoro amidodithioate PA0 N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA0 N-butyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA0 N-4-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid odithioate PA0 N-3-methoxybenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroami dodithioate PA0 N-3-trifluoromethylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phos phoroamidodithioate PA0 N-4-chlorophenylthiomethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)pho sphoroamidodithioate PA0 N-3-phenyl-2-butenyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoro amidodithioate PA0 N-1-methylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid odithioate PA0 N-4-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA0 N-4-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA0 N-phenyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioa te PA0 N-4-chlorophenoxymethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosph oroamidodithioate PA0 N-1-naphthylmethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroam idodithioate PA0 N-2-bromobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido dithioate PA0 N-2-chloro-6-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phos phoroamidodithioate PA0 N-4-methylthiobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoro amidodithioate PA0 N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA0 N-2-chloro-6-fluorobenzyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA0 N-3-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid othioate PA0 N-2-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid othioate PA0 N-3-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA0 N-3-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA0 R.sup.1 is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl; PA0 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5) alkyl, phenyl or benzyl; PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is methyl, ethyl, n-propyl, propenyl, or unsubstituted or substituted benzyl; and PA0 X, Y and Z are, independently, O or S. PA0 (H.sub.5 C.sub.2 O) P (O) (S--n--C.sub.3 H.sub.7) (N(C.sub.2 H.sub.5) (CHO)); PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(C.sub.2 H.sub.5) (CHO)); PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(C.sub.2 H.sub.5) (CHS)); PA0 (H.sub.2 C.sub.2 O) P (O) (S--n--C.sub.3 H.sub.7) (N(CH.sub.3) (CHO)); PA0 (H.sub.2 C.sub.2 O) P (O) (S--n--C.sub.3 H.sub.7) (N(CH.sub.3) (CHS)); PA0 (H.sub.5 C.sub.2 O) P (S) (S--n--C.sub.3 H.sub.7) (N(CH.sub.3) (CHO)); PA0 (H.sub.5 C.sub.2 O) P (S) (S--n--C.sub.4 H.sub.7) (N(CH.sub.3) (CHS)) PA0 (H.sub.2 C.sub.2 O) P (O) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.3) (CHS), PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 CF.sub.3) (CHO)) PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 CH.dbd.CH.sub.2) (CHO)); and PA0 (H.sub.5 C.sub.2 O) P (O) (S--3-pentyl)(N(C.sub.2 H.sub.5) (CHS)). PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 H.sub.5) (CHO)); PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 H.sub.5) (CHS)); and PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.3) (CHO)). PA0 R.sup.1 is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl or benzyl; PA0 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5) alkyl, phenyl, or benzyl; PA0 R.sup.3 is hydrogen; PA0 R.sup.4 is unsubstituted or substituted alkyl or unsubstituted or substituted benzyl; and PA0 X, Y, and Z are each O. PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 C.sub.6 H.sub.4 CN--4) (CHO)) PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 C.sub.6 H.sub.4 F--4) (CHO)) PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 C.sub.6 H.sub.4 CN--4) (CHO)) PA0 (H.sub.5 C.sub.2 O) P (S) (S--sec--C.sub.4 H.sub.9) (N(CH.sub.2 C.sub.6 H.sub.4 NO.sub.2 --4) (CHO))
The several Magee patents, U.S. Pat. Nos. 3,716,600, 4,049,679 (and continuation-in-part thereof, 4,110,443), 3,914,417, 3,845,172, 3,885,032, and 3,825,634, disclose insecticidal phosphoroamidothioates and phosphoroamidodithioates and methods of killing insects therewith. Column 18, lines 1-8 of U.S. Pat. No. 3,716,600 discloses broadly that, in addition to foliar application of the insecticidal compounds, one or more of the compounds may be applied in other liquid or solid formulations to the insects, their environment or hosts, for example, directly to plants or soil so as to effect control of insects coming into contact therewith. The compounds have the formula EQU (RY)(R.sup.1 S)P(.dbd.O)(N(R.sup.3)(C(.dbd.O)R.sup.2)
wherein R, R.sup.1, R.sup.2, and R.sup.3, respectively, broadly, are alkyl, alkenyl, alkynyl, and haloalkyl, and Y is O or S.
The abstract of Japanese Pat. No. 77012251 discloses N-acyl-O-alkyl-S-alkyl (alkoxy, alkylthio, alkenyl, phenyl, alkoxycarbonyl, cyano, carbamoyl)-phosphoroamidothioates having insecticidal activity and having the formula EQU [(R.sup.2 C(O)--N(H)]P(.dbd.O)(OR.sup.1)(S(CH.sub.2).sub.n R.sup.3).
Osborne, U.S. Pat. No. 3,399,213, discloses parasiticidal and fungicidal acylphosphoroamidate compounds having the formulas EQU (G)(G)P(.dbd.Z)[N(G"')--C(.dbd.O)--G"--C(.dbd.O)--[OG']
and EQU (G)(G)P(.dbd.Z)[N(Q)--C(.dbd.O)--G"--Q]
wherein G represents lower alkylamino, alkoxy, alkylthio, alkylphenyl, phenoxy, and substituted phenyl.
Braxton, Jr., et al., U.S. Pat. No. 3,511,635, discloses herbicidal organophosphorous-nitrogen compounds having the formula EQU (R.sup.1)P(.dbd.X.sup.1)(--XR.sup.2)(.dbd.N(CH.sub.2).sub.n)
wherein
Kishino et al., U.S. Pat. No. 3,760,043, disclose O-phenyl-S-alkyl-N-alkyl-phosphoroamidothioates which possess fungicidal, acaricidal, insecticidal, and nematocidal properties and have the formula EQU Aryl--O--P(.dbd.O)(NHR.sup.1)(SR.sup.2).
Schroeder, U.S. Pat. No. 3,657,426, discloses a method of controlling nematodes and other parasitic worm life existing in the soil at some stage of its life cycle by applying to the pests to be controlled or to the soil in which they live an effective amount of an O,O-dialkyl O-(1,2-dihydro-2-keto-1,6-dialkyl-4-pyridyl) phosphorothionate having the formula ##STR1##
Although the prior art discloses phosphoroamidothioate and phosphoroamidodithioate compounds having pesticidal, including insecticidal, activity, there remains a need for pesticidal compounds having improved pesticidal efficacy, and diminished detrimental effects such as mammalian toxicity and environmental waste, especially against soil insects such as the corn rootworm.
The prior art, including the several Magee patents described above which constitute the closest art known, do not provide any specific teaching illustrative of the insecticidal activity of the compounds therein disclosed when applied in the soil to protect against soil organisms. It is well known to those skilled in the art that organophosphates having a high order of contact insecticidal efficacy when applied to aerial, or foliar, portions of plants offer relatively little economic value as plant protectants when applied, or introduced, into the soil environment of the plants. Organophosphates tend to be susceptible to rapid degradative processes in the soil due to the combination of such factors as the hydrolytic action of soil moisture, unfavorable soil pH conditions, both of the above being exacerbated by the presence of soil microflora and fauna capable of rendering the insecticidal compound inactive. Application of a pesticide to the soil in ordinary agricultural practice does not necessarily or usually coincide with the presence of susceptible life stages of the target pest. For example, the hatching of insect eggs may be either delayed or it may occur over an interval of several days to several or many weeks. Insect ova are not generally affected by organophosphate pesticides. Thus, pesticidal compounds having satisfactory residual activity, especially in the soil--pesticidal compounds that retain their pesticidal efficacy under atmosphere conditions over an interval of several days to several or many weeks--are required in order to assure satisfactory protection of plants against soil insects. Further, it is highly desirable that such pesticidal compounds having activity persistent over an interval of several days to several or many weeks elicit control over a diverse selection of soil organisms that are agricultural pests.